Topic – Grignard, Alkane & Reduction

Section - I : Multiple choice question (Only one correct option) (MCQ)

1.

The formed products Z, Y, X are respectivley.

(a) (b)

(c) (d)

Solution – (a)

2. 2 – Phenylcycloprop – 2 – en – 1 – one is allowed to react with phenylmagnesium bromide and the reaction
mixture is hydrolysed with perchloric acid. The product formed is
(a) (b) (c) (d)

Solution – (D)

3. Which of the following reactions will give 20 chiral alcohol as one or more of major organic products?
(a) (b)

(c) (d) None

Solution – (b)
4. The end product of following reaction is

(a) 𝛼, 𝛽 − 𝑑𝑖𝑘𝑒𝑡𝑜𝑛𝑒 (b) 𝛼 − 𝐻𝑦𝑑𝑟𝑜𝑥𝑦 𝑎𝑐𝑖𝑑 (c) 1, 2 − 𝐷𝑖𝑜𝑙 (d) 𝛽 − 𝐻𝑦𝑑𝑟𝑜𝑥𝑦 𝑎𝑐𝑖𝑑

Soltuion – (B)
5. Observe the following raction sequence

(a) (b) (c) (d)

Solution – (A)

6. Observe the following sequence of reactions.

The product R is :
(a) (b)

(c) (d)

Solution – c

(𝑖) 𝐶𝐻3 𝑀𝑔𝐵𝑟

7. 𝑃ℎ − 𝑁 = 𝐶 = 𝑂 → 𝑃 𝐿𝑖𝐴𝐼𝐻4 > 𝑄
(𝑖𝑖 ) 𝐻2 𝑂

𝑃 𝑖𝑠 𝑃ℎ − 𝑁𝐻 − 𝐶 − 𝐶𝐻3 𝑎𝑛𝑑 𝑄 𝑖𝑠 𝑃ℎ − 𝑁𝐻 − 𝐶𝐻2 − 𝐶𝐻3

(a) ||
𝑂
 (b) P is 𝑃ℎ − 𝑁𝐻 − 𝐶𝐻3 and Q is

𝑃 𝑖𝑠 𝑃ℎ𝑁 = 𝐶𝐻3 𝑂𝐻 𝑎𝑛𝑑 𝑄 𝑖𝑠 𝑃ℎ − 𝑁𝐻 − 𝐶𝐻3

(c) |
𝐶−

𝑃ℎ − 𝑁𝐻 − 𝐶𝐻 − 𝐶𝐻3 𝑃ℎ − 𝑁𝐻 − 𝐶𝐻 − 𝐶𝐻3
(d) P is | and Q is |
𝑂𝐻 𝐶𝐻3

Solution - (a)
(𝑖) 𝐶𝐻3 𝑀𝑔𝐵𝑟
𝑃ℎ − 𝑁 = 𝐶 = 𝑂 →
(𝑖𝑖 ) 𝐻2 𝑂
𝐿𝑖𝐴𝐼𝐻4
𝑃ℎ − 𝑁𝐻 − 𝐶 − 𝐶𝐻3 →
||
𝑂
P(20 𝐴𝑚𝑖𝑑𝑒)

𝑃ℎ − 𝑁𝐻 − 𝐶𝐻2 − 𝐶𝐻3 "𝑄" (20 𝐴𝑚𝑖𝑛𝑒)

8. Which of the following reduction methods is not suitable for preparing an alcohol?
(a) 𝐶𝐻3 𝐶𝑂𝑂𝐶2 𝐻5 + 𝑁𝑎𝐵𝐻4 → (b) 𝐶𝐻3 𝐶𝑂𝑂𝐶2 𝐻5 + 𝑁𝑎/𝐸𝑡𝑂𝐻 →
𝑁𝑖
(c) 𝐶𝐻3 𝐶𝐻2 𝐶𝑂𝐶𝑙 + 𝐿𝑖𝐴𝐼𝐻4 → (d) 𝐶𝐻3 𝐶𝑂𝑂𝐻 + 𝐻2 →

Solution – (a)
𝑁𝑎𝐵𝐻4 does not reduce esters.

9.

What will be structure of X?

(a) (b)

(c) (d)

Solution – (b)
Because reagent is Li / 𝑁𝐻3
[i.e. 𝐿𝑖 + + 𝑒 Θ and 𝐻 − 𝑁𝐻2 ] there will be trans addition at both the ≡ bonds.

10. Compound on reduction with 𝐿𝑖𝐴𝑙𝐻4 followed by 𝐻3 𝑂 ⨁ produces

(a) (b)

(c) (d)
 Solution - (D)

11. Consider the following reaction

𝐶𝐻3 − 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻3 + 𝐵𝑟̇ →′ 𝑋 ′ + 𝐻𝐵𝑟,
| | X can be
𝐷 𝐶𝐻3

𝐶𝐻3 − 𝐶𝐻 − 𝐶𝐻 − 𝐶̇ 𝐻2 𝐶𝐻3 − 𝐶𝐻 − 𝐶̇ − 𝐶𝐻3

(a) | | (b) | |
𝐷 𝐶𝐻3 𝐷 𝐶𝐻3

𝐶𝐻3 − 𝐶̇ − 𝐶̇ 𝐻 − 𝐶𝐻3 𝐶𝐻3 − 𝐶̇ − 𝐶𝐻 − 𝐶𝐻3

(c) | | (d) |
𝐷 𝐶𝐻3 𝐶𝐻3

Solution – (b)

Most stable radical is formed.

12. In which compound heat of combustion is highest :

(a) (b) (c) (d)

Solution – (D)
C and D have higher no. of C atom and C has (e, e) structure in chair conformation which is more stable than D.

𝐾𝐻𝑆𝑂4 𝐿𝑖𝐴𝐼𝐻4
13. Glycerol → [𝐴] → [𝐵]. which of the following is not B
(a) Allyl alcohol (b) Acrolein (c) Acrylic acid (d) Propyl alcohol

Solution – (B, C)
 Section – II : Multiple select question (one or more than one correct options (MSQ)
14. Which of the following is / are correct for the given reaction?

(a) (b) (c) (d)

Solution – (c)

15. Which of these carbonyl compounds on reduction with Zn – Hg / HCl will give the same compound as product
(a) (b)

(c) (d)

Solution – (A, B, C)

On reduction will give

16.

(a) (b) 𝐸 𝑖𝑠 𝐶𝐻2 = 𝑂&14 𝐶𝐻2 = 𝑂

(c) (d)
Solution - (A, B, D)

𝐶𝐻3
|
17. 𝐶𝑙2 /ℎ𝑣
𝑃ℎ − 𝐶𝐻2 − 𝐶𝐻 − 𝐶𝐻3 ⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗
(𝑚𝑜𝑛𝑜𝑐ℎ𝑙𝑜𝑟𝑖𝑛𝑎𝑡𝑖𝑜𝑛)

Which statements is / are correct about photochemical chlorination of the above compound?
(a) The major product will be chiral carbon atom having optically inactive compound.
(b) The Intermediate free radical of the major product is resonance stabilised.
(c) The intermediate free radical is tertiary.
(d) The intermedaite free radical is planer, and stabilised by only hyperconjugation.

Solution – (A, B)
Free radical mechanism
𝑃ℎ − 𝐶𝐻2 − 𝐶𝐻 − 𝐶𝐻3
|
𝐶𝐻3
Give three type of alkyl radicals.

18. Which reaction is / are correct.

(a) (b)

(c) (d)

Solution – (B , D)
B and D are correct reactions.

19. Point out the following INCORRECT Grignard synthesis.

(a) (b)
 (c) (d)

Solution – (a, b, d)
A, b and d are incorrect Grignard synthesis.

20.

The correct statement about (I) and (II) are :

(a) The acid catalysed hydrolysis of (I) and (II) yields one product identical.
(b) For Wolff Kishner reduction (I) is the better reactant.
(c) (II) gives positive haloform reaction.
(d) Reduction by 𝐿𝑖𝐴𝐼𝐻4 forms a diol in both the cases.

Solution (a, b)

Wolff Kishner reduction is not used in presence of base sensitive group.

𝐸𝑡ℎ𝑒𝑟 𝐶𝐻3 𝑂𝐻
21. 𝑅𝑋 + 𝑀𝑔 → 𝑅𝑀𝑔𝑋 → 𝑛 − 𝐵𝑢𝑡𝑎𝑛𝑒
What can be R in the above reaction sequence?
(a) n – Butyl (b) sec – Butyl (c) n – Propyl (d) Isopropyl

Solution – (a, b)
R is 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝑜𝑟

𝐶𝐻3 − 𝐶𝐻 − 𝐶𝐻2 − 𝐶𝐻3

|

22. In which of the following reactions the product is optically inactive

(a) (b)

(c) (d)

Solution – (b, c)
Section – III : Comprehension / Paragraph based question (CBQ)
Comprehension # 1
Read the following reaction
2𝐶𝐻2 −𝐶𝐻𝑂
| 𝑁𝑎𝑂𝐻
𝑁𝑎𝑂𝐶𝑙 𝑀𝑔 𝐾𝑂𝐻 (𝑖 ) 𝐻2 /𝑃𝑑./𝐵𝑎𝑆𝑂4
𝑆→
𝐶𝑙
𝐶𝐻 ≡ 𝐶𝐻 → 𝑃 𝑄 → 𝑅 → 𝑇 ⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗ U&U
⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗
𝐸𝑡ℎ𝑒𝑟 𝐻2 𝑂 (𝑖𝑖) 𝐷𝑖𝑙. 𝐾𝑀𝑛𝑂4

23. ‘S’ in the above reaction

(a) (b) (c) (d)

Solution – (a)

24. ‘U’ is
(a) (b) (c) (d)

Solution – (a)

25. ‘Q’ is
(a) 𝐶𝑙𝑀𝑔𝐶 ≡ 𝐶𝑀𝑔𝐶𝑙 (b) 𝐶𝐻 ≡ 𝐶 − 𝑀𝑔𝐶𝑙 (c) 𝐶𝑙 − 𝑂 − 𝐶 ≡ 𝐶 − 𝑀𝑔𝐶𝑙 (d) 𝐶𝑙 − 𝑂 − 𝐶 ≡ 𝐶 − 𝑂𝐶𝑙

Solution – (a) (23 to 25)

Comprehension # 2
Considering the following reactions (I, II, III) and give your answer for following questions

26. If 𝐶𝐻3 𝑀𝑔𝐵𝑟 is taken in excess in reaction (I), how many moles of 𝐶𝐻3 𝑀𝑔𝐵𝑟 will be consumed in reaction
(a) 2 (b) 3 (c) 4 (d) 5

Solution – (B)
27. The product in the reaction (II) will be
(a) (b) (c) (d)

Solution – (D)

28. In which set of the reactions in (III) the product will be 20 alcohol?
(a) a, b, c (b) b, c, d (c) c, d (d) c, d, e
 Solution – (c)

Section – IV : Numerical Value Questions (NVQ)

29. An isomer of 𝐶5 𝐻12 gives total six isomeric products on monochlorination. Calculate the percentage yield of the
primary monochloride which is chiral. Consider the following relative reactivity of C – H bonds for chlorination.

Degree of C - H 10 𝐶 − 𝐻 20 𝐶 − 𝐻 30 𝐶 − 𝐻
Relative reactivity for 1 3 5
chlorination (RR)

Answer – (30)

𝐶𝐻3 − 𝐶𝐻 − 𝐶𝐻2 − 𝐶𝐻3

Primary monochloride can be | % yield of primary monochloride which is chiral = 30%
𝐶𝐻3
30.

The numbers of moles of 𝐶𝐻4 gas formed in this reaction is.

Solution - (5)
There are five protic hydrogen atoms available in the given molecule.

31. Observe the following experiment

If the reactant ‘P’ is ethyl chloride then the product R has the numbers of optically active compound :

Solution – (0)
𝑀𝑔
𝐶𝐻3 𝐶𝐻2 𝐶𝑙 𝐶𝐻3 𝐶𝐻2 𝑀𝑔𝐶𝑙
⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗
𝑒𝑡ℎ𝑒𝑟
𝑂 𝐶𝐻2 − 𝐶𝐻3
|| |
𝑅−𝐶−𝑂−𝑅′ 𝐻2 𝑂
→ → 𝐶𝐻3 − 𝐶𝐻2 − 𝐶 − 𝑅 (R).
|
𝑂𝐻
(Achiral)

32. of total monochloroproducts (with stereo isomers).

Solution – (8)

33.
 Solution – (3, 2)

𝐶𝑙2 𝐹𝑟𝑎𝑐𝑡𝑖𝑜𝑛𝑎𝑙 𝐷𝑖𝑠𝑡𝑖𝑙𝑙𝑎𝑡𝑖𝑜𝑛

𝑃ℎ − 𝐶𝐻 − 𝐶𝐻2 − 𝐶𝐻3 𝑝𝑟𝑜𝑑𝑢𝑐𝑡𝑠 → Fractions
⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗
ℎ𝑣
34. Number of fractions are :
|
𝐶𝐻3 (𝑅)(+)

Solution – (5)

35.

How many total isomeric reactants can be converted into given product by Wolff Kishner reduction.

Solution – (5)

36. How many alkenes (Be sure to consider the stereochemistry of the alkene) can be hydrogenated to form methyl
cyclohexane.
 Solution – (6)

37.

Find the total number of isomers formed in the end product.

Solution – (3)

38. Observe the following reaction and mention the number which show slowest and rate determine step.

(1) (2)

(3) (4)

Solution – (4)

39.

Total number of products in the above reaction :

Solution – (03)

Section – V : Column match Questions (CMQ)

40. Match the following considering the reaction of 𝐶𝐻3 𝑀𝑔𝐵𝑟 with the compounds in column A and products are
written in column B.

Column A Column B
(P) 𝐵𝑟 − 𝐶𝐻2 − 𝐶 ≡ 𝐶 − 𝐶𝐻3 (1) 𝐶𝐻3 𝐶𝑁
 (Q) 𝐶𝑙𝐶𝑁 (2) 𝐶𝐻3 − 𝐶𝐻2 − 𝐶 ≡ 𝐶 − 𝐶𝐻3
(R) 𝐶𝐻3 𝐶𝑂𝐶𝑙 (3) 𝐶2 𝐻5 𝐶𝑂𝐶𝐻3
(S) 𝐶2 𝐻5 𝐶𝑂𝑂𝐶2 𝐻5 (4) 𝐶𝐻3 𝐶𝑂𝐶𝐻3
(5) 𝑃ℎ𝐶𝑂𝐶𝐻3
Which of the following combination is correct :
(a) 𝑃 → 2; 𝑄 → 1; 𝑅 → 4; 𝑆 → 3 (b) 𝑃 → 3; 𝑄 → 2; 𝑅 → 4; 𝑆 → 1
(c) 𝑃 → 2; 𝑄 → 4; 𝑅 → 3; 𝑆 → 1 (d) 𝑃 → 4; 𝑄 → 3; 𝑅 → 1; 𝑆 → 2

Solution – (A)
𝐶𝐻3 𝑀𝑔𝐵𝑟
(𝑃 ) 𝐵𝑟 − 𝐶𝐻2 − 𝐶 ≡ 𝐶𝐻3 → 𝐶𝐻3 − 𝐶𝐻2 − 𝐶 ≡ 𝐶 − 𝐶𝐻3
𝑆𝑁 2
𝐶𝐻3𝑀𝑔𝐵𝑟
(𝑄) 𝐶𝑙𝐶𝑁 → 𝐶𝐻3 𝐶𝑁
𝑆𝑁 2
𝐶𝐻3 𝑀𝑔𝐵𝑟
(𝑅) 𝐶𝐻3 𝐶𝑂𝐶𝑙 → 𝐶𝐻3 𝐶𝑂𝐶𝐻3
𝐻3 𝑂+
𝐶𝐻3 𝑀𝑔𝐵𝑟
(𝑆) 𝐶2 𝐻5 𝐶𝑂𝑂𝐶2 𝐻5 → 𝐶2 𝐻5 𝐶𝑂𝐶𝐻3
𝐻3 𝑂+

41. Match the following

Column - I Column - II
(P)

(Q)

(R)
 (S)

Which of the following combination is correct :

(a) P → 2 ; Q → 1 ; R → 4 ; S → 3 (b) P → 2 ; Q → 1 ; R → 5 ; S → 3
(c) P → 3 ; Q → 4 ; R → 1 ; S → 2 (d) P → 4 ; Q → 3 ; R → 1 ; S → 2

Solution – (B)
(i) Formation of P is by MPV reduction
(ii) 𝑁𝑎𝐵𝐻4 /𝐻2 𝑂/ 𝐶2 𝐻5 𝑂𝐻 will reduce COCl group.
(iii) NalEtOH causes Boveault balnc reduction (Reduction of ester group)
(iv) 𝐿𝑖𝐴𝐼𝐻4 will then reduce acid group.

42. Match the following

Column I Column II
𝐿𝑖 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 (1) (𝐶𝐻3 )2 𝐶𝐻𝐶𝐻2 𝐶𝐻 (𝐶𝐻3 )2
(P) 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 → ?
⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗
𝐶𝑢𝑙

𝐿𝑖 (𝐶𝐻3)2 𝐶𝐻𝐶𝐻2𝐵𝑟 (2) 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝐻3

(Q) (𝐶𝐻3 )2 𝐶𝐻𝑙 → ?
⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗
𝐶𝑢𝑙

𝐿𝑖 𝐶𝐻3𝐶𝐻2 𝐵𝑟 (3) (𝐶𝐻3 )3 𝐶𝐶𝐻2 𝐶𝐻3

(R) 𝐶𝐻3 𝐶𝐻2 𝐶 (𝐶𝐻3 )2 𝐵𝑟 ⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗ → ?
𝐶𝑢𝑙

𝐿𝑖 𝐶𝐻3 𝐶𝐻2 −𝐵𝑟 (4) 𝐶𝐻3 𝐶𝐻2 𝐶 (𝐶𝐻3 )2 𝐶𝐻2 𝐶𝐻3

(S) (𝐶𝐻3 )3 𝐶𝐶𝑙 → ?
⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗⃗
𝐶𝑢𝑙
(5) (𝐶𝐻3 )3 𝐶 − 𝐶 (𝐶𝐻3 )3
Which of the following combination is correct :
(a) 𝑃 → 3; 𝑄 → 2; 𝑅 → 4; 𝑆 → 1 (b) 𝑃 → 2; 𝑄 → 1; 𝑅 → 4; 𝑆 → 3
(c) 𝑃 → 3; 𝑄 → 4; 𝑅 → 1; 𝑆 → 2 (d) 𝑃 → 4; 𝑄 → 3; 𝑅 → 1; 𝑆 → 2

Solution – (b)
All these reactions are corey house synthesis.

Section – VI : (3 Column) Match the list questions (MLQ)

Answer 4.43, 4.44 and 4.45 by appropriately matching the information given in the three Columns of the following
table.

Column 1 Column 2 Column 3

(I) Wurtz Reaction (i) 𝑅2 𝐶𝑢𝐿𝑖 (P) Acid sensitive groups, which
should not be present in the
reactant.
(II) Wolff Kishner Reduction (ii) 𝑁𝑎/𝑑𝑟𝑦 ether (Q)Both symmetrical and
unsymmetrical alkanes can be
 prepare by this method.
(III) Clemmensen’s Reduction (iii)𝑁𝐻2 − 𝑁𝐻2 / 𝐾𝑂𝐻 (R) Alkanes having odd no. of carbon
atoms can’t be prepared.
(IV) Correy-House Synthesis (iv) Zn – Hg / Conc. HCl (S) Base sensitive groups, which
should not be present in the
reactant.

43. 2 𝐶𝐻3 − 𝑋 → 𝐶𝐻3 − 𝐶𝐻3 What is the correct combination for the reaction :
(a) (III) (i) S (b) (II) (iv) Q (c) (IV) (iii) P (d) (I) (ii) R

Solution – (D)
𝑁𝑎 / 𝑑𝑟𝑦 𝑒𝑡ℎ𝑒𝑟
2 𝐶𝐻3 − 𝑋 → 𝐶𝐻3 − 𝐶𝐻3 This is Wurtz reaction.

44. What is the correct combination for the reaction :

(a) (III) (iv) S (b) (III) (iv) P (c) (II) (iii) S (d) (II) (iii) P

Solution – (c)

This is Wolff Kishner reduction, so base sensitive groups should not be present in the reactant.

45.

What is the correct combination for the reaction :

(a) (III) (iv) Q (b) (III) (iv) P (c) (III) (iv) S (d) (II) (iii) (P)

Solution – (B)

This is Clemmensen’s reduction, so acid sensitive groups should not be present in the reactant.
Answer Key Grignard, Alkane & Reduction_2024

1 A 9 B 17 A, b 25 A 33 3, 2 41 B
2 D 10 D 18 B, d 26 B 34 5 42 B
3 B 11 B 19 A, b, d 27 D 35 5 43 D
4 B 12 D 20 A, b 28 C 36 6 44 C
5 A 13 B, c 21 A, b 29 30 37 3 45 B
6 C 14 C 22 B, c 30 5 38 4
7 A 15 A, b, c 23 A 31 0 39 3
8 A 16 A, b, d 24 A 32 8 40 A